Southwest® flights from Kona (Island of Hawaii) to Chicago (Midway) from $357

Promo Code

Low fares from Kona (Island of Hawaii) to Chicago (Midway)

$

Kona (Island of Hawaii) (KOA)to

Chicago (Midway) (MDW)
Depart: 06/02/2026

One-way

Basic

From
$357
Seen: 16 hrs ago

Kona (Island of Hawaii) (KOA)to

Chicago (Midway) (MDW)
Depart: 04/21/2026

One-way

Basic

From
$367
Seen: 17 hrs ago

Kona (Island of Hawaii) (KOA)to

Chicago (Midway) (MDW)
Depart: 04/03/2026

One-way

Basic

From
$392
Seen: 2 hrs ago

Kona (Island of Hawaii) (KOA)to

Chicago (Midway) (MDW)
Depart: 06/02/2026

One-way

Choice

From
$407
Seen: 16 hrs ago

Kona (Island of Hawaii) (KOA)to

Chicago (Midway) (MDW)
Depart: 04/21/2026

One-way

Choice

From
$417
Seen: 17 hrs ago

Kona (Island of Hawaii) (KOA)to

Chicago (Midway) (MDW)
Depart: 06/15/2026

One-way

Basic

From
$432
Seen: 1 hour ago

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Explore flights from Kona (Island of Hawaii) to Chicago (Midway)

Apr 2026
From$367*
Seen: 17 hrs ago
One Way/Basic
May 2026
No result for this month.
Jun 2026
From$357*
Seen: 16 hrs ago
One Way/Basic
$367
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    • Range$367-$447

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Kona International Airport at Keahole
    Arriving at:
    Chicago Midway International Airport
    Distance:
    4221 miles

    Route Information

    42† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 42 weekly flights from Kona (Island of Hawaii) to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Kona (Island of Hawaii) to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Kona (Island of Hawaii) to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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